Tourists walking along shops, attractions, and food establishments on the boardwalk in Ocean City, Maryland. Editorial credit: eurobanks /

Maryland's Best Small Towns for a Weekend Escape

Maryland's unique geography, surrounded by beautiful bodies of water like Chesapeake Bay and Potomac River, make it an excellent escape for those who need it. Beyond boating and fishing, these waterways weave a thread through the soul of the state's best gems. Spirited towns like Ocean City and Easton flourish with charming waterside settings, while Chesapeake City boasts the historic Chesapeake and Delaware Canal. As one of the country's top producers of world-class seafood, Maryland is also a haven for foodies. Here are the top places for a weekend escape in the Free State.

Ellicott City

Ellicott City Historic District, Maryland, USA - Buildings constructed in the 1800s nestled in the valleys of the Tiber and Patapsco rivers.
Ellicott City Historic District, Maryland, USA. Editorial credit: Nicole Glass Photography /

Ellicott City, in its heart, is a small town but has the tells of a big city. Its downtown area, particularly Main Street extending to Frederick Road, will feel like a walkable postcard. It's lined with cute shops and galleries, like Bohemian House and Gott Folk, and restaurants, such as Syriana and La Palapa Grill and Cantina. You can cap the night off with a glass of old-fashioned rye whiskey at Ellicott Distilling Company or a microbrew at Phoenix Upper Main.

Weekenders looking for a quiet break can visit Patapsco Valley State Park. This 16,000-acre park has a well-maintained playground for folks traveling with their youngins, and with multitudes of shaded and lush areas, you can easily bring your favorite snacks for a nice picnic. Bonus for fur parents, the park is pet-friendly, too.

A visit to this dreamy town calls for an equally charming accommodation. The Wayside Inn, a bed and breakfast with gourmet breakfast options and luxurious amenities, is a top-notch choice among travelers.


Solomons Island, Maryland.
Solomons Island, Maryland.

Solomons or Solomons Island is a great pick for a serene getaway in Maryland. The town is surrounded by the Patuxent River and is popular among boating enthusiasts. Curious cats could first pop by the Calvert Marine Museum to get themselves properly acquainted with the region's fruitful past. Science buffs can also visit the Chesapeake Bay Biological Laboratory for insightful talks with brilliant marine biologists and their quest to protect the bay.

Annmarie Sculpture Garden & Arts Center is the ideal spot for afternoon strolls and for art fiends (and everyone else!) to check out unique installations and works.

Fancy the charm of the olden days? Solomons Victorian Inn cradled on the southern tip of the town close to the waters, is a fine accommodation just a few steps away from numerous shops and trendy dining joints.

North Beach

Homes on Chesapeake Bay, North Beach, Maryland, under a sunny blue sky

Homes on Chesapeake Bay, North Beach, Maryland.

If you enjoy beach towns with iconic boardwalks, North Beach will be right up your alley. This laid-back community is located right by the Chesapeake Bay; you can spend your weekend on the beach riding the waves, dozing off, or even fishing. Wetlands Overlook Park and Sunrise Garden are ideal spots for a relaxing stroll after a day out in the sun.

Maryland, at large, is a top producer of seafood in the country, and if you'd like a taste of the freshest catch, you can bring your whole crew for a feast at Neptune's Seafood Pub or Hook & Vine Kitchen and Bar.

The Blue Crab Beach House is one of the best places to stay if you wish to enjoy the bay, as the host often gives up to four beach passes. Club Carp North Beach is another ideal retreat if you are traveling with kids. For a more luxurious retreat with marina amenities, reserve a suite at The Inn at Herrington Harbour.

Ocean City

Aerial view of Ocean City, Maryland at sunrise with vacation properties.
Aerial view of Ocean City, Maryland.

Looking for a retreat right by the water? Ocean City might just be the perfect getaway for you. This resort town is sandwiched between the Atlantic and the Isle of Wight Bay. Its famous boardwalk on the southern end is almost three miles long and is lined with all sorts of entertainment, from the legendary OC Big Wheel at Trimper Rides to the Kraken at Jolly Roger.

For great eats, some of the most popular spots in town are Guidos Burritos, The Dough Roller, and Hammerheads Bar & Grill. Travelers looking for an electric night out filled with rock and roll will fit right in at Purple Moose Saloon.

Depending on where you plan to explore the most, you are spoiled for choice when it comes to accommodations. Fenwick Inn and Mad Men Beach House are highly-rated choices in the northern area, while mid-Ocean City is lined with more popular hotels like Best Western and Holiday Inn. If you prefer to stay near the boardwalk, Park Place and The Lankford Hotel are recommended.

Rock Hall

Middle-aged Caucasian couple sitting on a bench by the beach in Rock Hall, Maryland, with identical bikes parked next to them.
A couple sitting on a bench by the beach in Rock Hall, Maryland. Editorial credit: grandbrothers /

Rock Hall in Kent County may be small, but it's home to a thriving marina lifestyle and community that attracts tourists from around the country. It's an ideal escape for folks looking to pass the time by the water.

At Haven Harbour Marina, you can rent a boat for your group, dine at the waterfront Passages Bar & Grill, and enjoy luxurious amenities. For an equally picturesque marina with fewer crowds, you can try Gratitude Marina or Swan Creek Marina on the western side of the town.

While there are a slew of excellent dining options in Rock Hall, Waterman's Crab House and Harbor Shack top the list if you are craving the signature Maryland crab. For a night of entertainment, The Mainstay will keep you bopping to groovy tunes all night.

Osprey Point Inn and Inn at Haven Harbour are some of the top accommodation choices if you fancy waking up to the sights of the bay. If you'd like to stay close to the happenings on Main Street, Cinnamon By The Bay is an ideal retreat.


View of Thompson Park and downtown Easton, Maryland, historic seat of Talbot County on the Eastern Shore.
Thompson Park and downtown Easton, Maryland. Editorial credit: grandbrothers /

Art lovers will find Easton worthy of a weekend stay. This postcard-worthy town in Talbot County is home to numerous galleries, such as the Academy Art Museum and Troika Gallery. The Avalon Theatre is a top-notch venue for those who enjoy live entertainment. Local crafts and Amish products are also on full display at Amish Country Farmers Market.

If you enjoy boating or simply taking a nice walk while ringing in the sunset, it might be worth visiting Easton Point Marina or Easton Point Park. Tourists could also pop by beloved local dining spots like Rise Up Coffee Roasters and Doc's Downtown Grille.

Easton has its fair share of unique places to stay for weekenders. Hummingbird Inn is a dog-friendly, Victorian-style bed and breakfast with a wraparound veranda to welcome the sunrise, while Tidewater Inn is a lavish escape with an on-site bar.

Chesapeake City

Homes on Chesapeake Bay, North Beach, Maryland, under a sunny blue sky.
Homes on Chesapeake Bay, North Beach, Maryland, under a sunny blue sky.

Chesapeake City, the only Maryland town situated along a working canal, is worth a look when it comes to quick getaways. Curious minds can visit the Chesapeake and Delaware (C&D) Canal Museum, have a private boat party, or go on a sunset cruise. Afternoons can be spent walking the length of the Ben Cardin C&D Canal Trail and even crossing into Delaware!

For a nice grub in a unique waterside setting, Schaefer's Canal House delights diners with its signature crab cake sandwich and seafood nachos. The Bayard House and Prime 225 also won't disappoint discerning palates.

Take your stay up a few notches by staying at Ship Watch Inn, a waterfront retreat boasting suites with an outdoor deck to enjoy the scenic views. If you want to splurge on an upscale lodging that has a romantic atmosphere, The Blue Max Inn is ideal.

Discovering Solitude In Maryland

Maryland isn't shy about its unique towns tailored to every preference. If you are fond of places with historic ambiance, discover Easton's art galleries or Chesapeake City's canal path. Adventure lovers can hike Patapsco Valley or kayak around Solomons Island, and foodies can feast on fresh seafood in North Beach or Rock Hall. Start packing your weekend bags because Maryland has a slew of charming towns ready to sweep you off your feet.

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